


Curiosity kills even the snake

by ContrivedCircus



Category: Durarara!!
Genre: Blackmail, IzaShiki, Kink Meme, M/M, One-Shot, Toys, Vibrators
Language: English
Status: Completed
Published: 2014-11-21
Updated: 2014-11-21
Packaged: 2018-02-26 11:02:33
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,000
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/2649593
Author URL: https://archiveofourown.org/users/ContrivedCircus/pseuds/ContrivedCircus
Summary: <blockquote class="userstuff">
              <p>(One-Shot IzaShiki based on a kink meme) </p><p>Izaya blackmails Shiki into having sex with him.</p>
            </blockquote>





	Curiosity kills even the snake

Izaya crosses his legs, a smirk upon his lips as he curiously watches the Yakuza across from him. Seated in the middle of his living room, the two sit in complete silence as Shiki’s mind twists and turns from Izaya’s words.  
Of course, today was a good day to have sent Namie home early, assuming the elder accepted his terms, things were about to become very interesting. 

A glare still fixated upon his features, Shiki stares daggers at Izaya. “If I accept your terms, you will destroy the evidence? I have your word on this?” 

Chuckling to himself, Izaya nods with a wave of his hand. “Not to worry, Shiki-san. If I get what I’m after, all the information concerning your back dealings will be erased.” 

Earlier that week, the Informant had spent days tirelessly gathering proof of the Yakuza’s betrayal’s. While nothing he had done was particularly devastating for the Awakusu-kai, it was still against the organization. 

‘He could easily lose a finger... or two for this.’

A deep sigh is released by Shiki who then leans forward. Intertwining his fingers, the Yakuza settles his chin upon his hands.  
“Fine, I accept your terms. But I want proof that the information is being destroyed. I also want your word that nothing occurring here tonight will shared with another human or non-human being.” 

Tilting his head, the Informant’s crimson orbs stare into Shiki’s brown ones. He could see the frustration behind his gaze, the anger.

Yet, something about that look had his dick twitching with an obscene desire.

“I give you my word, Shiki-san. Now then… I want you to remove your clothes while I get a few things.” Rising from the couch, the Broker smirks down at the Yakuza. Of course he had accepted his offer, Izaya had made sure that his options were slim. Options with a desirable outcome that is. 

As the Informant steps away from his entertainment area, he can hear the quiet sound of clothes ruffling. Surely the Yakuza was moving slowly, taking his time. Shiki’s pride was indefinitely damaged, he currently resembled a kicked dog.  
But it was that within itself that had Izaya so excited. This was going to be so much fun.

It takes him a few minutes to return downstairs, in Izaya’s hands is a small box.  
Within the box is lube, as well as a small egg shaped vibrator with a cord attached leading to a remote.  
Before him sits the Awakusu executive, stripped to his boxers with a cigarette between his fingers. The man himself retains a mostly blank expression, his lips tilted in a frown as he notices Izaya’s return.   “Informant-san..” Shiki nods before pressing the cigarette filter to his lips.   “It’s probably a good idea that you smoke now, I imagine it’ll be rather difficult soon.”   Setting the box down on the coffee table, Izaya takes a few steps towards Shiki, eyes sweeping over his body. From where he’s standing, he can catch a glimpse of a portion of the Yakuza’s rather impressive tattoo. Black and blue ink winds up his shoulders, ending in a point just before his arm. Izaya can tell the singular point he can see, likely leads to a far larger piece. 

“Tell me, Shiki-san.. Have you ever had sex with another man before?” Reaching into the box, Izaya extracts the small bottle of lube.   “I don’t believe detail of my sexual history is part of the deal, Orihara-san.”   Smirk growing wider, Izaya gestures Shiki to stand with his fingers.   “Boxers off, I want you to bend over with your back facing me, knees on my couch.”   The elder’s face doesn’t change despite the rather lewd instructions. Stubbing his cigarette out in the ceramic ashtray on the coffee table, he stands and does as Izaya requested.   Kicking Shiki’s boxers away, the Informant steps closer until he’s just behind the Yakuza. He had been correct, the executives back was covered in a beautifully designed tattoo. Black, blue and red ink paints his skin, curving over his back but ending just before his ass or arms.   The Informant considers commenting on it for a moment, changing his mind as he opens the lube bottle.   “Well if you won’t disclose your sexual history for me; I’ll find amusement in your reactions. After-all, actions speak louder than words, right Shiki-san?”

Clear lube slips over two of Izaya’s fingers, shining against the dim lighting of his apartment as he closes the lube bottle. Dropping the small container back into the box, Izaya places his non-lubed hand on Shiki’s back, pressing one lubed finger against Shiki’s entrance.   Pressing his finger through the tight ring of muscles, the Informant slowly sinks his finger in. Beneath his hand, Shiki’s muscles tighten, his head dropping slightly as the Broker’s finger delves completely inside.   “If you relax, it’ll feel better.” Izaya teases, sliding his finger out again.   Slowly now, his finger thrusts into the tight hole, crimson orbs drawn to the scene as his cock twitches for a taste. 

However, the Informant has more in plan than a simple fuck.   Increasing the speed of his thrusts, the Informant adds a second finger. Muffled groans escape the elder as Izaya’s fingers curl, rubbing over his prostate with each thrust. If Shiki had any experience with men in the past, it certainly wasn’t as the bottom. 

Pressing against his walls, the Broker presses against the cluster of nerves, admiring the sounds the Yakuza emits with each push.    
“You’re fairly apt to this aren’t you, Shiki-san?” Izaya teases, drawing his fingers back as he add’s in a third one.   Less interested in being gentle, the Informant swiftly thrusts all three digits inside. The executive at his mercy arches his back, a slightly louder groan resounding as Izaya quietly chuckles to himself.   The younger male’s free hand grips the executives hips tighter, leaning towards Shiki’s ear as he speaks.   “You’re enjoying this aren’t you? My fingers in your tight ass. It’s so lewd, you should see the way you’re ass swallows them up.”   Pulling his fingers out, Izaya’s lubed fingers reach into the box, drawing out the small egg vibrator before positioning it at Shiki’s entrance.   “Before I continue, I want to ask you something.”   Pausing for a brief moment, the Broker pushes the toy until it only slightly penetrates the elder.   “How loud do you think you can moan for me?” 

 

Pushing the toy in all the way, Izaya’s fingers force it in as far as his fingers can reach before he withdrawals his digits.   “Just a small change of pace now. I want you on your knees in front of me.” 

Shiki moves slowly, removing himself from the Informant’s black couch as he settles on his knees in front of Izaya.   With the remote in one hand, the younger male’s free hand moves to his belt, undoing it swiftly before undoing the buttons on his pants.   “I assume you know what you’re current task is, yes?”   Shiki glares up at the Broker, eyebrows furrowed as he lifts both of his hands.   One of the executives hands moves to Izaya’s hip, gripping tightly as his free hand moves to withdrawal the informants dick from the confines of his boxers.   “Nothing to say? Well, then why don’t you go ahead and occupy your mouth.” Izaya was pushing his limits with his words and he knew it. It was likely he would pay for this in the risk level of his jobs later down the line, however at the moment he didn’t care. 

The Yakuza’s hand wraps around Izaya’s hardened dick, a glare still fixated upon his face as he hesitates for a moment. Pressing his lips against the head of the Informant’s length, Shiki’s mouth slowly parts as he takes the broker’s cock in his mouth.  
 The warmth now encompassing his dick has Izaya’s face tinting a slight red. The executives tongue winding around the sensitive head combined with his hot breath and the glare fixated upon his face, serves to only further fuel Izaya’s arousal.   Free hand moving to Shiki’s hair, Izaya slowly turns the toy on the lowest setting. Instantly the Yakuza reacts, his mouth no longer working as slowly as he grips the Informant’s hip harder.   “Oh? You like that don’t you?” Lips curling, the Informant’s fingers tightly wind into Shiki’s hair, his hips bucking as he slowly thrusts into the elder’s mouth.   It felt good, the heat, the moisture, he wanted more but he didn’t want to overdo it.   After-all, Shiki is a business partner.   Turning the toy up a bit more, Izaya finds pleasure in Shiki’s facial expressions, the muffled moans as he takes all of Izaya’s dick into his mouth.   Releasing his hold on Shiki’s hair, the Yakuza’s free hand moves to grip the base of Izaya’s dick. He seemed to be working harder to maintain his glare, however fruitless of an effort it is.   “Fuck..” Izaya mutters as the elder man’s tongue winds around his dick. He could feel himself throbbing, twitching for release. It had been so long since Izaya had even touched himself, and Shiki was certainly not a slow learner.   Moving his hand to the back of Shiki’s head, Izaya’s fingers wind in a bit lighter now, maintaining a grip on his head as he continues to thrust into the hot, wet, chasm.   Once he feels like he can’t wait anymore, the Broker’s fingers hold tightly to Shiki’s hair, forcing him to take all of his length as he cums in his mouth. The Yakuza’s fingers tighten on Izaya’s hips, his eyes wild as Izaya holds his mouth on him. The feeling was amazing, his body alight with electricity as he spills himself into the elder’s mouth. Perhaps he should forego fucking the man, and simply abuse his mouth for a few hours?    
As Izaya rides out the end of his orgasm, he releases Shiki’s hair, allowing the man to draw his head back. As he does so, the elder man pulls away, coughing as he swiftly moves to wipe his mouth. 

“What the hell?” The executive questions, his glare holding true as he repeatedly attempts to swallow the sticky substance.   “My rules today, Shiki-san.” Izaya laughs, turning the vibrator up.   The Yakuza’s dick twitches against the action, his face unchanging aside from a slight twitch in his eyebrow. He could act as though it didn’t affect him all he wanted, but Izaya refused to settle until he earned a reasonably loud moan from him.   “Why don’t you move back onto the couch for me? The same position as before.”   Izaya’s hand moves down to his length, rubbing it lightly as Shiki lifts himself from the Informant’s living room floor.   Perhaps he should’ve turned on some music? But then again, Izaya sort of enjoyed the dull buzz of the vibrator in Shiki’s ass.   The Yakuza physically flinches as he moves, the toy certainly shifting with each movement as he gets back into his original position.   Given the height difference, Izaya had chosen a position that would allow him to stand and not have to face his business partner.   “You’re quite good at following directions, Shiki-san. I’m impressed.” His teases are followed by another condescending chuckle. His laughs surely getting on Shiki’s nerves by now.  However, the Informant fails to care. Turning the toy up more, Izaya grinds his hips against Shiki’s ass.   “I should tell you what I’m going to do right?” 

Grinding harder, Izaya can almost feel the toy vibrating against his slowly hardening dick.   “I’m going to shove my dick in you, I’m going to shove it in you with the toy. Say, Shiki-san, have you ever been fucked with a vibrator in your ass?”   The Informants hands move to the Yakuza’s hips. Shiki’s head drops against the back of the couch, his hands balled into fists as he groans against the vibrations.   Izaya wanted to fuck him so badly, and yet he had to wait. Patience is not exactly a strong suit of the Informants.   “I never realized you were…. so lewd..” Shiki laughs, his head turning to catch Izaya’s gaze.   “Consider this a rare event, Shiki-san. I’m not often interested in this sort of thing. You just so happen to be lucky contestant number one.”   “I’m… honored, Orihara-san.” The annoyance in his voice brings a smile to Izaya’s lips. Shiki’s pride was clearly damaged, damaged by the toy in his ass, damaged by the cum he had been forced to swallow. Izaya was getting the exact amount of control that he wanted.   Rubbing his dick harder against the Yakuza’s ass, Izaya’s fingers squeeze the warm skin.  
The elder beneath him drops his head again, his back arching as he begins groaning again. 

“Getting close?” Izaya questions, a mischievous grin upon his lips as he bends to look at executives dick. 

The Yakuza says nothing, groaning a bit louder as his entire body begins to tremble. Taking one hand, Izaya reaches around, wrapping his hand around Shiki’s length and beginning to pump. 

“Don’t…. touch me… Informant..” Shiki groans just as his orgasm finds it’s escape. Moaning louder now, Shiki cums to Izaya’s hand pumping his dick and the toy vibrating in his ass. It was clear that the Yakuza’s pride hurt even more now, his eyes squeezed tightly shut as his body shakes with the remnants of a hard finish.   Bringing his free hand away from Shiki’s dick, Izaya grabs his own cock. Although he had just finished, his dick had already gotten so hard. 

“Ah?”    
Releasing his dick, Izaya reaches for the lube bottle again. Opening the small container, he dribbles a bit more onto his hand before dropping the bottle into the box once more.   “Now then.. I wonder.. How loud can you be, Shiki-san?” Wrapping his hand around his length, Izaya strokes himself slowly, spreading the lube over his length before positioning himself at Shiki’s tight entrance. 

As the head of his dick touches the exposed muscles, Izaya can feel the light vibrations from the toy he had left there. The remote still in one hand, The Informant slowly pushes himself inside.   Shiki’s back immediately arches from the action. Izaya’s own face flushing red as Shiki’s ass tightly swallows his dick.   “I wonder…” Izaya begins, slowly pushing his dick in further. It felt wonderful to sink himself into the elder man. His cock being so tightly squeezed sent a shudder down his spine, desire alight in his eyes as he imagines himself cumming in his tight ass. 

“Will you moan louder as I fuck your ass? Or will you pathetically try to disguise your own pleasure whilst creating another mess on my couch?”   Sheathing himself completely, the Broker grinds his hips against the Yakuza’s ass. Hot, wet, tight, and the vibrations… All of it was driving him crazy.   Izaya draws his hips back, his dick brushing against the vibrator as he does so. 

Pulling back until he’s almost completely out of him, the younger male slams himself back into the elder, earning a loud groan from Shiki.   “Oh so you do like it rough?” Gripping the executives hips tightly, Izaya roughly thrusts himself in and out of his twitching hole. The vibrations encompass his dick so completely, furthered by the tight walls gripping him.   Izaya himself can’t help but moan against the feeling. He hadn’t expected it to feel this good, but the idea of fucking Shiki for forever wasn’t sounding too bad at the moment.  The Broker pushes his dick in as far as he can get it, rolling his hips as he listens to the ever growing sounds of pleasure and pain from the elder man beneath him.  
“Your ass is squeezing my dick so hard. Are you doing that on purpose?” The Informant asks, his breathing becoming more labored with each rough thrust.   “Shut… up.. Informant-san…” Laughing, Izaya continues to roughly thrust his dick into the abused hole. He’s fucking an executive for the Awakusu-kai, That singular fact within itself is amusing. Shiki-san who always maintained a rather stoic expression, who always seemed so put-off or unaffected by Izaya’s charm…  Smirking again, Izaya looks down at the elder man. 

‘Shiki-san is currently moaning as I fuck his tight ass. I wonder if he frowns even while getting fucked?’

Thrusting harder, Izaya groans as his dick brushes against the small vibrator. The sound of skin-on-skin filling the spacious apartment along with Shiki’s moans, growing in volume with each rough thrust.   “Nnh..” The Informant’s hands grip tighter to the hot skin, eyes drawn down to the tattoo on Shiki’s back as he shoves his dick into Shiki as far as he can.   Leaning forward, the Broker’s body shudders as he spills himself inside of the elder man whose body trembles as it finds it’s own release for the second time. 

As each of them ride out their orgasm, Izaya can’t help but smile. He had gotten exactly what he wanted with little to no consequence thus far.  
Of course that spoke nothing of what may happen later.   Slowly, Izaya withdrawals his dick, cum seeping from the bright red, abused hole.   Shiki himself wastes little time, reaching around, two fingers slip in and draw the egg out by the cord. A frown once again fixated upon Shiki’s face as he drops the egg onto the couch, still vibrating. 

Turning to Izaya, the elder man seems to loom over the slightly smaller male who retains an enraging amount of smugness.   “Now, I fulfilled my end. I want you to destroy the information.”   Shiki’s eyes hold Izaya’s, a serious note in his voice as he makes no move to re-dress himself; despite the way Izaya is already fixing his belt.  
Turning away from Shiki, Izaya takes a few steps before lifting his hands in a shrug. Turning foot, the Broker faces the elder once again with a sly grin curving his lips.   “Now-now, Shiki-san.. You should have known that I never had any _proof_ you were engaging in any sort of _undesired_ behavior.”


End file.
